This was a very enjoyable experience. If you want to learn about the history of the island, this is the way to go. We went with Ranger Don who was outstanding. He provided lots of information at numerous stops along the way. Make sure you buy your ticket at least a few weeks in advance since it gets booked up. Our group was about 25 people ranging in age from about 7 to 65 years. Since this is a half day experience, it might be difficult for the very youngest visitors.
As others have said, you should not wear flip flops, but you can wear good sneakers... you don't need hiking boots. On our hike it did not rain, and there is almost always tree cover, so even though it might be warm and humid, it is not uncomfortable. If you are coming over from St. Thomas on the ferry, there are places to get breakfast, snacks, and food and water to bring in a pack for the walk. Also bring a bathing suit and towel for the swim at the end. There is a bathroom where you can change into your bathing suit.
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